Drug overdose remains a leading cause of death in the US, with growing rates attributable to illicit fentanyl use. Recent HIV outbreaks among people who inject drugs (PWID) and service disruptions from COVID-19 have renewed concerns on HIV resurgence. We examined the relationship between fentanyl use and three injection-related HIV risk behaviors among PWID in Baltimore City (BC) and Anne Arundel Country (AAC), Maryland. PWID (N = 283) were recruited to the study through targeted sampling at street-based locations in BC and AAC from July 2018 to March 2020. Receptive syringe sharing (RSS) [adjusted odds ratio (AOR): 2.8, 95% confidence interval (CI): 1.2–6.3] and daily injecting (AOR: 1.9, 95% CI: 1.0–3.6) were associated with injecting fentanyl and cocaine together. Fentanyl availability and COVID-19 bring new HIV prevention challenges, particularly among those who inject fentanyl with cocaine, highlighting the importance to expand and sustain harm reduction, prevention, and treatment services for PWID to reduce HIV and overdose burden.